


The Annex Files

by wildfire98



Category: The Office (US)
Genre: Alternate Universe - The Office Fusion, F/M, Flashbacks, Kissing, Love, Office Sex, Semi-Public Sex, relationships
Language: English
Status: In-Progress
Published: 2018-02-27
Updated: 2019-01-25
Packaged: 2019-03-24 21:26:20
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 3,841
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13819755
Author URL: https://archiveofourown.org/users/wildfire98/pseuds/wildfire98
Summary: Tina need her training at Dunder Mifflin Scranton to go well. But after meeting her trainer Toby, she quickly is challeneged to not reveal her past relationship with Mr. Flenderson to the rest of the office. Can she survive the summer next to this man?





	1. Chapter 1

**Author's Note:**

> This is something I have been wanting to write for a while and have a plan for this piece. I always felt like Toby never getting to have a love interest on the show was a missed plot line. (The thing with Nelly was weird.) Tell me what you think about the end. Much love guys!

                I wasn’t sure what to expect when I walked into the office of Dunder Mifflin for the first time. Being fresh from the Human Resources program at the New York offices I was worried about how I would be in a real office setting. I was warned before I left about the Dunder Mifflin offices. On paper they were the most profitable branch, but people would always give me a raised eyebrow when I told them where I was going to do my on the job training.

None the less I wanted to make my best impression on my new coworkers. I left my apartment that morning in my best skirt and blouse hoping that my appearance would make me look more professional than I felt. I smoothed them down with the back of my shaky hand one last time before entering the office.

Behind the desk at the entrance was a woman with a warm smile that looked up to greet me. “Hi, how can I help you?”

“Hi I’m Tina, I am here to train with Mr. Flen-“

“TINA!” A loud voice from behind me made me jump higher than I thought I could.

Turning around I found a goofy looking gentleman in a dark blue suit grinning ear to ear standing in the door of an office off to the left of the desk. He started to laugh as he walked towards the desk. My purse did not survive the scare and the contents of my bag went flying across the floor. The lady, Pam, seemed annoyed and gave me another warm smile that had a hint of annoyance this time.

“Michael this is Tina, I believe she is here to train with Toby.”

“Oh well then I’m sorry that he is going to MURDER YOU.”

After quickly scooping up my purse I looked back at him and I started to feel the blood rush to my cheeks. I wasn’t sure what he was getting at, but I felt like he was joking. I was never really good at ‘riffing’ with someone, and I was hoping this wasn’t what he was expecting from me. He stood with his arms out wide like he was posing for photo- or waiting for me to hug him. I wasn’t sure what was worse.

“From… from the boredom? He is going to kill you with lameness…” He looked at me with another goofy grin.

Coughing into my hand I gave a small grin, “Oh… Well I’m sure that isn’t true.”

“WELL, you haven’t met him yet. Anyway- I am Michael Scott, your boss and soon to be best friend. And this is everyone!” He turned to the rest of the room and spread his arms out wide to introduce me to the office.

Looking across I saw the rest of my coworkers spread through the office. Most of them looked older than me, and this intimidated me. I was the youngest at the training in New York, and now in this office I felt my age of twenty-three was by far the youngest in the group. However, everyone looked friendly. Well, except for the gentleman sitting not too far from me with wide wire framed glasses and a reserved gaze. He gave me a quick up and down before standing to address Michael.

“Michael I thought we agreed to not hire anymore sales people. I don’t think we need more competition as it is.”

                “That is true Dwight. Conveniently, our young prodigy here is going to be training with gross Tobey for the summer and won’t intervene with your sales.”

                “Its okay Dwight. No one is going to steal your clients. Your beets however are up for grabs.” A younger looking man about thirty at the desk next to Dwight’s smiled up at me and raised his hand to shake.

                “I’m Jim, this is Dwight. He is going to say things like that its okay to not respond to him.”

                “No one would steal our beets. They are well taken care of thank you. Mose sets the traps.”

                “Yeah things like that. Don’t respond to those.”

                Reaching down I shook his hand and after Michael started to introduce me to everyone around the office giving me way too much information about my coworkers. The kind of information that I had been learning in my training should stay with employees, not to be announced to new members by the boss. Once he introduced me to the last person, I was confused on where Mr. Flenderson was and tired of hearing about who had slept with who in the office. Mr. Scott was really milking this interaction for all he could.

                “This has been great to meet everyone, but I thought I was here to train with Mr. Flenderson?”

                “Ah! Yes now our tour will lead us to the annex where you will be working.”

                Leading me through the kitchen Michael led to back offices. I started to feel the butterflies in my stomach as I walked into the room. I hoped I was ready for this job. I needed this training to go well. Jobs were scarce, and I really did like this profession. Dunder Mifflin had paid me while I was in training and I felt I had a lot to prove.

                “TOBY!” Michael shouted.

                Turning around in his chair Mr. Flenderson faced me and I wanted to drop to the floor and die. He looked annoyed by Michael’s greeting, but when we locked eyes I could tell he was feeling the same as me. His face fell, and his mouth hung open. I didn’t need Michael to introduce me to Mr. Flenderson. I knew him very well.

                My last week in New York, I had slept with Mr. Flenderson.


	2. Chapter 2

**Summary for the Chapter:**

> Tina makes her way home, but it never is just that easy is it?

**Notes for the Chapter:**

> Hi guys. It was been just under a year since I posted this story. I just want you to know that I am going to finish it, and am actually serious about being more active on this site. I had to get my life sorted before I could dedicate time to my passions. Hopefully you are here to read as I am here to write! (oh god that was corny.) Alright, I hope you enjoy!

“You guys want to grab a drink to celebrate?”

  
Walking down the steps from the corporate building that Friday, I felt relief flood me. Scotty, Jemma, and I had spent the last month learning from the HR director to prepare for our on the job training. Day after day, we had to sit and watch video after video, trying to absorb everything we could about our future profession. We started out with four people but after the first week someone dropped out, and I couldn’t blame them. I wanted this job but being in an office day after day is not for everyone.

  
“I don’t know Scotty, its never just a drink with you.” Jemma said, placing her hand on his shoulder.

  
Jemma was the oldest of us by about ten years. She had two kids and had been a stay at home mom before her husband had passed suddenly. Scrambling for work to support her kids and herself, she applied to Dunder Mifflin and I knew I was going to miss her. She came everyday with the best attitude that someone could have for what she has been through. I struggled with staying positive and she always helped reassure me when I doubted myself during the training.

  
“Come on Jemma, you can get the babysitter to stay for another hour.”

  
Scotty was young and only took this job to get his father off his back. He worked in another New York high rise and Scotty had told us time after time that he was on his back to get a real job. To me he was just a privileged brat, but I did genuinely like him. It was hard to listen to him during lunch about his trips to Turks and Cacaos when I had hardly left New York.

  
“You two go ahead. I can’t think of a better way to celebrate than with my kids.”

  
Jemma pulled us both in for a quick hug and I could see she looked she was going to cry.

  
“You guys. I had to move quickly after Thomas died to make sure my kids and I were going to be okay. I can’t tell you how thankful I am to have you guys with me.”

  
I couldn’t help but pull her in for another hug. I didn’t want stop working with Jemma. I was going to miss her dearly. Waving goodbye, she walked down to the end of the street and around the corner.

“Alright are you going to tap out on me too?”

  
I laughed and considered my options. I really needed to go home and back, but I could use the distraction. We really did have a reason to celebrate.  
“Okay Scotty, lead the way.”

\------------

After the fourth round I found my way towards the door as I looked back to see Scotty lip locked with a man who had bought us our third round of drinks. I wanted to say goodbye to him, but I would just text him the next morning. As I left the bar I headed towards my apartment and I could feel my heels tap uneasily against the concrete. Jemma was right, it was never just one drink with Scotty. I had never held my liquor well, but today's excitement and skipping lunch made me especially vulnerable. This became obvious as my shoulder made contact with the side of a well-dressed woman clutching her small dog in her hands.

“Watch it Bitch!” she growled as her tiny dog did the same.

  
“Oh, I’m sorry mam.” I mumbled into the collar of my coat as I tried to regain my balance.

  
I would miss living in New York, but I knew it was time to move on. I never did well in crowds, and that was all this city had become. I needed to find somewhere I could finally relax and leave my family problems behind me. It seemed like the start of a Hallmark Movie, but I knew my life was somewhere else, I just had to find it. Maybe a man? I chuckled to myself. Now I was really trying to live out my Hallmark fantasy.

  
Turning the corner with my building in sight I started to feel relaxed. All I wanted to do was get my clothes off and take a hot bath. Thinking of all the packing I had to do tomorrow to get ready for the U-Haul coming the next day made me anxious. I shouldn’t have waited so long to pack my place, but I had always been a procrastinator and true to form instead of spending the night putting boxes together I planned on testing out the bath bombs I purchased last weekend.

  
I blamed this daydreaming distraction for taking away my focus from my whiskey legs, as the tip of my heel caught on the edge of the curb and my face quickly connected with the cement. Feeling the instant pain, I laid on the cement for five seconds deciding if it was even worth it to get up. My knee was throbbing as it had taken the brunt of the fall, but I could already feel the warm spill of blood on my head. I had so much hope hours ago, and now here I was laying on a dirty New York sidewalk. This felt like an illusion to something but I wanted to focus on getting up before I thought about that.

“Ar- are you okay?” a monotone voice above me rang out.

Craning my neck to the side I saw a middle-aged man dressed in a brown suit and coat holding a briefcase looming over me. He looked worried and I knew I needed to get myself up. Pushing my arms to my side I was able to lift my torso to a sitting position.

“Oh. You are, uhm- bleeding.” The stranger said as he reached into his pocket and pulled out some crinkled-up napkins to hand to me. I reached for them but found myself reaching back.

“Those aren’t used, are they?” I finally uttered. He showed a small smile of sympathy in response.

“No, I just grabbed a slice of pizza. These are just the ones I didn’t use. Can I help you up?”

Shaking my head to let him know it was okay, I felt his arm wrap around my waist and I was brought back to a standing position. Instantly my knee buckled, and he had all my weight in his arms. He smelled like after shave and soap. If anything, he smelled just like he looked- plain. Wait, was I smelling this man? I must have hit harder than I thought.

“Are you able to stand?” he said as I snapped myself out of my daze.

“I think I hit my knee too hard. Can you take a look?” Even I was shocking myself for asking, but I knew I wasn’t going to be able to check if it was okay. I was beyond embarrassed, but it wasn’t going to get any more embarrassing from this point.

I felt his fingers lightly touch my knee and I winced with pain.

“I’m not a doctor but I don’t think it’s broken. Can you walk at all?”

He removed his arm from my waist and I tried to take one step but instantly fell back to his side.

“Oh dear.” He gasped as I fell into him. Grabbing his jacket for support I let out a quick gasp in the direction of his face and I watched as his nose crinkled.

"Did you have a little too much to drink tonight?"

Oh, so it can get more embarrassing. Not only was I holding bloody napkins to my scratched forehead, I couldn’t walk. On to of that, he probably thought I was some drunk who couldn't hold her liquor. While that had some truth to it, I didn’t want to be his problem anymore. Unless I could drag myself to my apartment elevator, I was going to need to ask him for help.

“Sir, I live right here. I know I have bothered you enough, but would you mind helping me into my apartment? I promise I wouldn’t ask if I thought I could do it on my own.”

  
He gazed up at my building and looked back at me. I knew he didn’t have to say yes, but I wasn’t exactly sure how he was going to say no to my pathetic request.

  
“Okay. Just lean against me I can help.”

  
As we started to walk towards the main door I wrapped my arm around his shoulder for support as he held my waist. Reaching into my purse for my keys I couldn’t help but be cynical.

“Hallmark movie my ass.”

“What?”

“Nothing.”

**Notes for the Chapter:**

> This had to be the transition piece to get to where I wanted to really be with this story. I redid it ten times, until I realized I just needed to split what I wanted into the next chapter. The plan is to post at least once a week. I'm not sure how long it will go on for, I have a idea in my head, and I want to see it out! Hope you enjoyed this chapter. Much love, and thank you for the kind words!


	3. Chapter 3

**Summary for the Chapter:**

> Leading her sidewalk hero up to her apartment, Tina finds out more about him.

**Notes for the Chapter:**

> Ha, remember that note I left that said I would post once a week? Well... a month later here we are. I did get a lot of comments last chapter so I just want to say thank you! I love writing but am still learning a lot! Hope you enjoy!

With a thud I landed on the end of my tiny couch, a throb still radiating from my knee. My skirt was ruffled and dirty and my brand-new blazer had a rip in the elbow. The thing that worried me the most was the irony behind falling so hard just when I had hope for a new start in a new town. In what was turning out to be the most awkward night of my life I looked up to the man that had helped standing above me, obviously not knowing what to do next. 

I hadn’t really looked at him while I was trying to walk against his side into my building. I wanted to take a better look at his face in the elevator but staring at someone in an elevator who you don’t even know who picked you up off the street is probably against any social norms that apply to a situation as this. From the brief memory I remembered him as plain but looking up I was caught off guard by his large blue eyes. In all honesty he looked like Eeyore- but in a handsome, sullen kind of way. 

“So I should go, I think?” He questioned, as if he wasn’t sure if leaving me was a jerk move or not. Though he had no reason to stay, I’m sure he didn’t want to feel like he was abandoning me. 

Before I could answer I spotted drops of blood on the corner of his button up shirt. This was the side he supported me with and it must of came from the cut on my head when I would lean against him. Following my gaze, he looked over at his own shoulder and pulled at his shirt where the stain was. 

“Oh my gosh I am so sorry. Here-“ I tried to stand but my knee started to hurt again. Letting out a wince I knew I was probably down for the count the rest of the night.

“Oh it’s really fine, my hotel is only a couple of blocks from here and I am just going back-“

“No really I just have a couple of oversized shirts in my drawer-“

“It’s really not a big deal-“

I reached out and grabbed his hand and he stopped protesting me. I didn’t want to look desperate, but I would still be on the sidewalk if it wasn’t for his kindness. The least I could do was have him leave here with a shirt that had no blood on it.

“Please, let me give you a shirt. It is just a shirt. For a thank you.”

He looked back down at me and gave the smallest of smiles let go of my hand “Okay.”

Trying one last time I picked myself off the couch. Ignoring the throb, I hobbled over to my dresser, conveniently close since I lived in a studio, and pulled open the second drawer. Pulling out a white oversized shirt I made my way back to him.

“There is a bathroom right over there if you want to go change.” I said as I handed over the clothing. With a small nod he set down his briefcase and went to the bathroom, the door shutting with a small thud behind him.

Funny enough this was the first time a man had been in my apartment in many months. To be fair this was the first time anyone had been in my apartment for a while, as I consumed work and didn’t find much time for anything else. The last person here was a wine night a month and a half ago with Jemma leaving Scotty to babysit her kids. A disaster that happened to be because he let her kids drink soda and eat ice cream all night, so she preferred to be at home with her kids instead of going out. Which was fair. Honestly, I was jealous of her life. Even though she was doing so much alone, at least she had people who needed her at home. 

I took a moment while he was in the bathroom to use the kitchen sink and a small mirror to access the damage to my head. I knew I didn’t have a concussion, but I just wanted to make sure I didn’t need any stiches. But a quick clean off showed the blood was the worst of the cut, and it had already closed up on it’s own. Emerging from the bathroom my stranger was now clothed in my shirt and had his shirt folded in his hands.

“I have some stain removal I can put on that. I would care to guess you probably didn’t bring that with you if you are staying at a hotel.”

“I would try to say no but I feel like you would just talk over me.” He said with almost no personality in his voice. I would have taken offence if I hadn’t seen the corner of his mouth turn into another weak smile.

“You learn quick.”

Grabbing his shirt, I slowly made my way to the small closet beside the kitchen that housed my cleaning supplies. Finding the Clorox pen, I popped the cap and started to apply it to his shirt.

“I guess I should ask for your name, so when I replay this story in my head over and over from embarrassment at least I will know what to call you.”

“I’m Toby.” He stated, and I felt that name suited him well. 

“Well hello, my name is Tina.”

“Are you going somewhere?” Turning to look back at him I saw he was gesturing towards the unfolded boxes that were laying against the wall, packing tape and scissors laid on the floor in front of them. 

“Yes, I start a new job next week. I move in a couple days.”

“Happy to be leaving the big city?” and this question I didn’t know how to answer, so instead, I decided to ignore it. 

“Why are you in town? You mentioned you were staying at a hotel?”

Instead of an answer I heard footsteps coming towards me. Spinning quickly around, I found he had moved himself to stand only a couple feet away from me. I didn’t expect him to be so close, and in an attempt to step back I bent my knee and caused it to buckle. I tried to grab the counter, but my hands fumbled. Quickly I felt Toby’s arms grab to support me for the second time that night. Only this time, he stood in front of me, one arm around my waist, the other on my back. 

I didn’t even know what to say. Looking back up at him I saw his big eyes trying to read my face. Was this the same guy who didn’t even want to take my shirt? His smell of after shave and soap filled my senses again, and I felt the flush quickly spread to my cheeks. Nothing about him said bold, but here I was in his arms.

“I… I don’t mean to assume.” He stammered, his boldness starting to waver, “And I don’t think you even planned this, but if you wanted to…” he trailed off. 

I couldn’t help but grin, the thought of my ‘plan’ of falling outside my apartment to lure older men into my small studio was beyond hilarious. But did I want this? Because while I had never been one for sleeping with strangers, I had to admit it had been a long time. But with Eeyore? I didn’t know. 

“Can I ask… why did you think I am up for this?” 

Blushing he looked to the side breaking eye contact, “Well my plan wasn’t to have you fall into my arms as I walked over here, but you just seem to keep ending up there.”

“But there was a plan?” I said as he reinstated eye contact. 

“I hadn’t written it all out yet, but yes.” Oh god, Eeyore had a good smile. 

So here I stood with an older man in my apartment, his arms as my only means of preventing myself of slipping onto the floor yet again. He had presented me with an option and was waiting for my okay. Was I making a mistake or was I only preventing myself from living one more true New York night? 

Breathing in I decided to approach it how I approached most of my life.

“Fuck it.” I said, and pushed my mouth onto his.

**Notes for the Chapter:**

> I know this Toby seems a lot bolder then the real character, but there is a plan here. I would say I plan on having another chapter up soon, but I feel like I shouldn't promise anything anymore, but I am doing my best! Thank you for reading!


End file.
